Vitamin d2 double compounds



; Patented Se t. 39, 1941 UNITED STATE s PATENT OFFICE vrramm m nounnn coMroUNns one Linsert,-Wuppertal-Elberield, Germany, as.- signer to Winthrop Chemical Companyrlnca New York, N. Y., a corporation of New York No Drawing. Application June 22, 1989, Serial Q No. 280,582. In Germany November 22, 1938 v k 3Claims.

This invention relates to vitamin D2 double compoimds. As it is known er osterol is converted into an antirachitically highly active transformation product by chemically active irradiation, particularly lay-ultraviolet irradiation.

The transformation product which has been prepared in pure form and which has been detected innatural vitamin D containing materials has been called vitamin D2.

The vitamin D1, immaterial whether produced from natural sources or by irradiation of ergos- I terol, shows the disadvantage that it is sensitive to oxygen Onstorage without special precautions the vitamin Do in pure form as well as in preparations, for instance solutions or mixtures with inert ingredients. is changed and-therefore the antirachitic eillcacy is gradually decreased.

In accordance with thepresent invention it has been found that the.vitamin D: forms double compounds with sterols oi the group consisting of cholesterol, cholestanol, coprosterol, sitostanol, and stigmastanol and that the sensitiveness of vitamin D; in the double compounds is considone day, washed with a 70 percent aqueous-aceo1. zoo-391.2)

The new vitamin D: sterol double are stable and may be r unchanged from suited solvents. Their less sensitiveness against oxygen allows a more convenient hen-.- dling of vitamin D2. The vitamin emcacy'is not diminished and corresponds to the vitamin D2.

content. The following example without, however, restricting it thereto.

Example 1 g. of vitamin D2 and cholestanol are dissolved in 70 cc. 01' hot acetone and thereto 30 cc. of water are added. The precipitate of at first not pronounced crystalline appearance is-changed after some hours into a mass oi needles fineas a hair, which is filtered with suction on standing for tone and dried'in vacuo. Yield: 90-95 percent,

erably decreased, the vitamin D efficacy is' preserved and corresponds to the vitamin .D: content. The greater stability 0! the double compounds allows a more convenient handling oi compounds melting point 104406", speciflc'rotary power A corresponding double compound is obtained by using instead of cholestanol the equivalent 7 The double compound,

thus formed has a melting point of 116' and a quantity of sitosta'nol.

specific rotary power Eln=+54 in acetone. 7

I claim: 1. Double compounds of vitamin D: with a sterol selected from the group consisting oi.

cholesterol, cholestanol, coprosterol, sitostanol, and stigmastanol.

' 2. The double compound of vitamin D: with cholestanolrepresenting thin needles melting at 104-106 and showing the specific rotary power [a]n= +54 in acetone.

3. The double compound of vitamin D: with s itostanol melting at 118 and showing the speciiic rotary power [ln- -+54 in acetone.- 0'1'10 LTNBERT.

compounds illustrates the invention 

